191330-56-0

Basic information

• Product Name: EZM-K
• Synonyms: (3R,4S)-1-(4-Fluorophenyl)-3-[3-(4-fluorophenyl)-3-oxopropyl]-4-(4-hydroxyphenyl)-2-azetidinone;Ezetimibe Ketone;EZM-K;(3R,4S)-1-(4-Fluorophenyl)-3-[3-(4-fluorophenyl)-3-oxopropyl]-4-(4-hydroxyphenyl)azetidin-2-one;EzetiMibe 3-Oxo IMpurity;Monophenyl phosphite diisooctyl;(3R,4S)-1-(4-Fluorophenyl)-3-(3-(4-fluorophenyl)-3-oxopropyl)-4-(4-hydroxyphenyl)azetidin-2-on;Ezetimibe Impurity 16(SCH57871)
• CAS NO: 191330-56-0
• Molecular Formula: C₂₄H₁₉F₂NO₃
• Molecular Weight: 407.41
• Product Categories: Chiral Reagents;Intermediates & Fine Chemicals;Metabolites & Impurities;Pharmaceuticals
• Mol File: 191330-56-0.mol
• Article Data: 16

Chemical Properties

• Boiling Point: 656.149 °C at 760 mmHg
• Flash Point: 350.627 °C
• Appearance: white crystalline solid
• Density: 1.325
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.615
• Storage Temp.: 2-8°C
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• PKA: 9.72±0.30(Predicted)
• CAS DataBase Reference: EZM-K(CAS DataBase Reference)
• NIST Chemistry Reference: EZM-K(191330-56-0)
• EPA Substance Registry System: EZM-K(191330-56-0)

Safety Data

• Hazardous Substances Data: 191330-56-0(Hazardous Substances Data)

Usage

Chemical Properties

White to Off-White Solid

Uses

Phase-I metabolite of Ezetimibe (E975000).

InChI:InChI=1/C24H19F2NO3/c25-17-5-1-15(2-6-17)22(29)14-13-21-23(16-3-11-20(28)12-4-16)27(24(21)30)19-9-7-18(26)8-10-19/h1-12,21,23,28H,13-14H2/t21-,23-/m1/s1

Upstream product

• 1501-26-4 methyl 4-(chlorocarbonyl)butyrate 
• 99395-88-7 (S)-4-phenyl-2-oxazolidinone 
• 133472-27-2 4-fluorophenylzinc chloride 
• 70627-52-0 4-benzyloxybenzylidene-N-(4-fluoro)phenylanisidine 
• 123-08-0 4-hydroxy-benzaldehyde 
• 371-40-4 4-fluoroaniline 
• 3382-63-6 (E)-(4-hydroxy-benzylidene)-(4-fluorophenyl)-amine 
• 149437-76-3 5-(4-fluorophenyl)-5-oxopentanoic acid 
• 189028-93-1 (S)-1-(4-fluorophenyl)-5-(2-oxo-4-phenyloxazolidin-3-yl)pentane-1,5-dione 
• 1185883-41-3 (S)-3-(5-(4-fluorophenyl)-5,5-dimethoxypentanoyl)-4-phenyloxazolidin-2-one 
• 163222-33-1 ezetemibe 
• 460-00-4 1-Bromo-4-fluorobenzene 
• 1593542-72-3 C₃₅H₄₃F₂NO₄Si 
• 1159183-23-9 C₃₂H₂₅F₂NO₅ 

Downstream Products

• 1478664-18-4 (3R,4R)-1-(4-fluorophenyl)-3-((S)-3-(4-fluorophenyl)-3-hydroxypropyl)-4-(4-hydroxyphenyl)azetidin-2-one 
• 163222-33-1 ezetemibe 
• 954109-26-3 (3R,4S)-4-(4-(trimethylsilyloxy)phenyl)-1-(4-fluorophenyl)-3-[3-(4-fluorophenyl)-3-oxopropyl]azetidin-2-one 
• 857506-68-4 1-(4-fluorophenyl)-3-(R)-[2-(4-fluorobenzoyl)ethyl]-4-(S)-[4-(t-butoxycarbonylmethoxy)phenyl]azetidin-2-one 
• 163222-32-0 (3R,4S)-1-(4-fluorophenyl)-3-[3-(4-fluorophenyl)-3(S)-hydroxypropyl]-4-(4-benzyloxyphenyl)-2-azetidinone 
• 163380-16-3 (3R,4S)-1-(4-fluorophenyl)-3-[(3R)-3-(4-fluorophenyl)-3-hydroxypropyl]-4-(4-hydroxyphenyl)-azetidin-2-one 
• 1159183-23-9 C₃₂H₂₅F₂NO₅ 
• 1042722-98-4 (3R,4S)-1-(4-fluorophenyl)-3-[3-(4-fluorophenyl)-3-oxopropyl]-4-[4-(trityloxy)phenyl]azetidin-2-one 

Relevant articles and documents

Ezetimibe intermediate and synthesis method thereof

The invention provides a new ezetimibe intermediate and a preparation method thereof. The preparation method comprises: (1) converting 4-(4-fluoro-benzoyl)-butyric acid into 4-[2-(4-fluoro-phenyl)-[1,3]dithiolan-2-yl]-butyric acid through a un-separated intermediate compound; and (2) carrying out acylation on chiral oxazolidone by using the 4-[2-(4-fluoro-phenyl)-[1,3]dithiolan-2-yl]-butyric acid to obtain the oxazolidone derivative VI. According to the present invention, the route is simple, cheap and efficient, and the obtained product has advantages of less impurity, high purity, and high yield.

Intermediate compound of ezetimibe

The invention provides a novel intermediate compound of ezetimibe and a preparation method thereof. The preparation method comprises a step of converting 4-(4-fluoro-benzoyl)-butyric acid into 4-[2-(4-fluoro-phenyl)-[1,3]dithiolan-2-yl]-butyric acid by using an unseparated intermediate compound. The method provided by the invention is simple in route, low in price and high in efficiency; and in order to better protect functional groups, the method employs the selectively removable protective group, so the method has the advantages of few impurities, high product purity and high product yield.

Preparation method of ezetimibe and key intermediates thereof of lipid-lowering drugs

The invention relates to a preparation method of ezetimibe and key intermediates thereof of lipid-lowering drugs. The preparation method is applicable to industrial production.